Synthesis of α-amino tetrahydropyranyl-, tetrahydrothiopyranyl-, 4- and 3-piperidinyl-phosphonic acids via phosphite addition to iminium ions

被引：21

作者：

Rabasso, Nicolas ^{[1
]}

Louaisil, Nicolas ^{[1
]}

Fadel, Antoine ^{[1
]}

机构：

[1] Univ Paris 11, Lab Synthese Organ & Methodol, UMR 8182, Inst Chim Mol & Mat Orsay, F-91405 Orsay, France

来源：

TETRAHEDRON | 2006年 / 62卷 / 31期

关键词：

ONE-POT SYNTHESIS; ASYMMETRIC-SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; AMINOPHOSPHONATES; DERIVATIVES; ENAMINES; ANALOGS; KETONES;

D O I：

10.1016/j.tet.2006.05.016

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

alpha-Amino cyclobutyl-, cyclopentyl-, cyclohexyl- and 4- and 3-heterocyclohexyl-phosphonates were efficiently prepared from carbocyclic and heterocyclic ketones, by nucleophilic addition of phosphite to the iminium ion formed by in situ condensation of these ketones with benzylic amines. Cleavage of the benzyl groups and acidic hydrolysis of the resulting a-amino heterocyclohexyl-phosphonates gave, in a three-step sequence from ketones, new 4- and 3-heterocyclobexyl-phosphonic acids. (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：7445 / 7454

页数：10

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